Palladium‐Catalyzed/Norbornene‐Mediated CH Activation/ N‐Tosylhydrazone Insertion Reaction: A Route to Highly Functionalized Vinylarenes

A straightforward method for the synthesis of highly functionalized vinylarenes through palladium-cata- lyzed, norbornene-mediated CH activation/carbene migra- tory insertion is described. Extension to a one-pot procedure is also developed. Furthermore, this method can also be used to generate polysubstituted bicyclic molecules. The re- action proceeds under mild conditions to give the products in satisfactory yields using readily available starting materi- als. This is a Catellani-Lautens reaction that incorporates dif- ferent types of coupling partners. Additionally, this reaction is the first to demonstrate the possibility of combining Pd- catalyzed insertion of diazo compounds and Pd-catalyzed CH activation.